One Friday night last fall, 50 well-dressed guests piled into an apartment in Hell’s Kitchen for a party celebrating Sheela-Marie Padgett, a 57-year-old former dancer with the New York City Ballet.

Waiters passed drinks before a buffet dinner of fancy Indian food was presented. Then came a chocolate cake from the Erotic Bakery made in the shape of corseted showgirl with a male appendage. It was sliced up and served to the crowd.

Which was fitting enough, because the following morning, Sheela — formerly known as Bruce — was scheduled to fly to Scottsdale, Ariz., for the last major procedure in her transition from male to female: gender reassignment surgery.

One by one, friends made their way over to the Nakashima-style wood dining table to offer congratulations. Almost unanimously, they noted that Bruce had been cynical, withdrawn and biting, while Sheela is soft and effervescent.

“It’s true,” said Ms. Padgett, who stands 5 foot 7 inches tall (when not in heels), wore a black lace top, and, with her hair done in a Raphaelite style, looked rather like the portrait that would emerge if John Singer Sargent were alive today to paint Madonna. “My friends were all frightened of me. I was a nasty person. I was so unhappy. It tainted all my relationships.”

Lori Ogle, another friend, said: “It’s really brave to do what she’s doing and it’s even braver because it’s so late in life. We were born the same year. I don’t know what I want to change, but this is inspiring. It’s like, ‘Go ahead, it’s not too late.’ ”

Awareness of transgender issues has surged over the last year. Laverne Cox, a star of the television show “Orange Is the New Black,” appeared in June on the cover of Time. Janet Mock chronicled her transition from male to female in the memoir “Redefining Realness,” which landed last spring on the New York Times best-seller list. Transgender models like Andreja Pejic have walked the runways in New York and Milan. And major retailers like Barneys are using transgender men and women in their ad campaigns.

But it took Amazon’s popular and acclaimed TV series “Transparent,” about a septuagenarian father of three who is coming out as trans (which coincided with frenzied coverage of Bruce Jenner’s drastically changed physical appearance) to shed light on a largely undiscussed segment of the transgender population: those who undergo a gender change later in life, sometimes even in their 60s and 70s, after decades of feeling not fully whole.

Coming out as transgender is not easy for anyone. But the issues are particularly thorny for those trying to reconfigure a central tenet of identity decades after building an adult life with family and career.

Social changes have a tendency to take root among the young, and to then trickle up years (sometimes decades) later. To be in transition around the time you qualify for AARP membership is to be on some level a paradox; a person newly born at a seasoned age.

Additionally, these late transitioners grew up in an era of rigid gender stereotypes, which they have been both oppressed by and in some cases internalized. A great number of them are married and have children who struggle to accept that the person who raised them is now becoming someone new.

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Rachel Sorrow, 64, of San Francisco transitioned around 60. She remains married to her spouse, though they date other people.Credit
Preston Gannaway for The New York Times

There are pragmatic as well as physical challenges, too, particularly for the older population of trans women (which refers to those born with men’s anatomy and who have since transitioned). Men’s jaws and shoulders widen over time, making a more “womanly” shape hard to achieve. Hair grows on their bodies while disappearing from their scalps, necessitating hair transplants or wigs.

All of which has profound emotional consequences for a group of people coming to terms not only with their genders but with the indignities of aging and impending mortality. Many will not be beautiful, like the young transitioners they watch on TV. Many will not “pass.”

“After I went on hormones, there was a letdown,” said Barbara, 63, who lives on the Upper East Side and agreed to talk to a reporter on the condition that her last name not be used. “I thought, ‘Where do I go now?’ I’m not going to look like a movie actress in her 20s or 30s. I’m not going to look like Laverne Cox.”

Today, she goes to a support group at Sage, the largest organization for older LGBT people. “No one there is dating,” she said.

Still, the pull to live as a person wants, even for a short time, even under reduced circumstances, remains powerful. Some people interviewed said they waited to retire before transitioning so as not to disrupt or destroy their careers. Others chose to push forward after the deaths of their parents or after their children had left the nest.

But invariably, they said that they had given enough, pretended enough, and wanted to claim the years remaining as their own. The entirety of their bucket list was to finally become themselves.

As Ms. Padgett tells it, she lived the first part of her life assuming that the pull to be female would go away. Her father was a Baptist minister in Mississippi. Her mother taught first grade. When she came to New York and became a dancer, she thought that she had found her calling, a world that was more open and tolerant.

She hung out with Andy Warhol at Indochine and spent late nights at Studio 54 and the Peppermint Lounge.

And yet during all the years she was a member of one of the world’s most famous ballet companies, she stood off to the side, wanting not to be the prince in “Swan Lake,” but Odette, the female swan.

It didn’t happen. Instead, after she turned 50, she found herself increasingly lonely and isolated. Then, in 2007 and 2008, her parents died in quick succession. She began to think of what she characterizes (in stronger language) as the “what the hell” years.

There was a small inheritance. A friend who had had gender reassignment surgery more than 20 years before went in for facial feminization surgery. “It was a big success,” Ms. Padgett said. “It completely changed her appearance.” Soon, she began telling people that she was transitioning.

Though the reaction to Ms. Padgett’s transition has been largely positive, the process nevertheless has been arduous, and filled with roadblocks that may not have existed had she made the leap earlier.

“Your grandmother looks more like your grandfather than she did while they were younger,” said Dr. Jeffrey Spiegel, a plastic surgeon in Boston who works largely on trans women and who treated Ms. Padgett. “The eyebrows drop, the nose changes, cheeks get more flat, the upper lips get longer, the jaw gets wider, skin quality deteriorates.”

“Dr. Spiegel redid my forehead,” Ms. Padgett said. “I had a very masculine brow bone, so he softened that. He raised my eyebrows so that there’s more space between my eye and my eyebrows. He cut the skin inside my lids to take away the old skin. He did a rhinoplasty to make my nose smaller and more delicate. He raised my upper lip so that there’s less space between my nose and my upper lip. He put in cheek implants and chin implants, and he did a tracheal shave and a lower neck and face-lift.”

The total cost for Dr. Spiegel’s work was $53,000. In addition, Ms. Padgett has had several years of painful electrolysis treatments to stop hair from growing on her face and body. Almost nothing related to Ms. Padgett’s gender transition was covered by her health insurance company, including her gender reassignment surgery and breast implants. With those three things added on, she estimates that the cost of transitioning physically was about $100,000. “I am broke,” she said.

Many trans people older than Ms. Padgett describe growing up in a time when there was really no vocabulary to even describe what they were.

“The only word was ‘transvestism,’ nothing was known of this at all,” said Bobbi Swan, 84, of Clinton, Mich., just north of Detroit. She transitioned at age 72.

After high school, deeply in the closet, Ms. Swan went to the Massachusetts Institute of Technology, got her degree in aeronautical engineering, and then served in the Air Force during the Korean War.

In 1954, she went to work at Ryan Aeronautical, where one of her jobs included flying target drones over China during the Eisenhower administration. She became a member of the National Rifle Association, donated to numerous Republican candidates, married three different women, had two children, ran a hunting preserve and, in the ’90s, secretly edited a magazine for transvestites called “Our Way.”

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“I think it’s safe to say that the employment I had would prohibit any sign of cross-dressing or anything like that,” Ms. Swan said. “I would have lost my job. The main customer is the Department of Defense. It was totally out of order.”

But by 2000, she had retired. Her children were grown. Her parents were no longer alive. It was time, she decided, to make a change she had long dreamed of.

So three years after Ms. Swan began taking hormones and dressing daily as female, she underwent gender reassignment surgery in Thailand. She paid for it mostly through a $5,000 check sent by one her sons that came with a note from him that read: “Sometimes the most important thing in life is finding oneself.”

That level of acceptance can be the exception. Stephanie James, a 64-year-old trans woman in St. Louis, said she is pleased that she is no longer living a lie (“It’s been worth every penny,” Ms. James said), but the reaction from her three sons was dispiriting. She told her youngest two sons in 2007. “They were bewildered,” she said. Her oldest son found out a week later and stopped speaking to her. They remain estranged. “I have not even met my grandbaby,” she said.

In 2009, she was fired as a strategic account manager at Graybar Electric, where she had worked for five years, during which time she transitioned. (Carrie Johnson, director of corporate and marketing communications at Graybar, said Ms. James’s departure was an “individual personnel matter” and declined further comment, saying, “I’m sure you can understand.”)

In her last two years at Graybar, Ms. James said, she earned $125,000 with benefits and bonuses. This year, working as a live-in caregiver to an 86-year-old woman, she earns $480 a week, plus health care. “You do the multiplication,” Ms. James said.

Over time, Ms. James has come to a number of awakenings not just about transphobia, but about sexism in general — dynamics she did not understand during 50-plus years living outwardly as a man.

“The loss of a position in a white male society is subtle but omnipresent,” Ms. James said. “I remember, before I was let go, I was in a corporate meeting and one of the V.P.’s said, ‘Who brought the bagels?’ No one had. So the V.P. says, ‘Stephanie, would you mind running out to pick them up?’ It was pouring down rain! We could all see it. There were windows on three sides of the conference room. That kind of stuff never happened before I transitioned. It happened all the time after.”

Gretchen Lintner, 58, lives in the San Francisco Bay Area. Shortly before she was laid off from her job at a commercial real estate firm, an executive there said to her, “Don’t you people just go somewhere new and start over?”

On a recent Friday, she was sitting in the lobby of a hotel near Union Square in San Francisco. She arrived wearing a Chanel-inspired blazer from Coldwater Creek, a Jones blouse, Gap jeans and a pair of alligator-patterned pumps. Her hair was long and blond and she wore silver hoop earrings. Nevertheless, as she walked in, the doorman greeted her by saying, “Hello, sir.”

“That’s how I go through life,” she said. “It’s the small oppressions that you get that you just have to be able to deal with.”

“The hardest thing,” she continued, “is working for less money and being bumped off my career track because of being a woman, because of being a trans woman, because of the 2008 economic dislocation. I don’t blame anyone, but it’s a fact. And I’m over 50 and it’s hard for any individual over 50 to find employment.”

Other things have changed as well. Today, Ms. Lintner dates both men and women. “For me, the parts are negotiable,” she said. “My sexual attraction was always toward women, and then as I transitioned I became more interested in men.”

For many, aspects of sexual identities shift. Language fails. There is a contingent of “transbien” relationships, the common term among LGBT types for what happens when two trans women get together. Straight men become straight women. Lesbians become gay men. This is what happened with Eugene Potchen-Webb, 60. He transitioned at 50 from female to male and, after having been a lesbian for many years, discovered he was into guys. “It was a surprise to me,” he said.

Rachel Sorrow is a 64-year-old San Francisco-based architect and amateur stand-up comedian who remains married to her spouse, though they date other people and sleep in different bedrooms in the apartment they share in the Castro.

“When I’m having sex with a man, I feel 100 percent a woman, and when I have sex with women I slip back into male roles,” Ms. Sorrow said. “I always thought if you are a guy and you have a sex-change operation and you’re still dating women, you’re a lesbian, because you look like a woman and you’re dating them. It’s a relatively reasonable assumption unless you know a lot of trans people.

“In our case, I think it just doesn’t apply. I have way more flexibility than that. Trans means to move back and forth, like transportation, and I think that’s just part of it.”

But having a progressive attitude about sex and self-expression doesn’t preclude clinging to ideals that are anachronistic and even a little bit sexist. Many older trans women grew up in “Mad Men”-era houses where women were accessories and children were supposed to speak when spoken to. And sometimes these tendencies are absorbed and play out in ways feminists sometimes find disconcerting.

“I do feel like sometimes I have to be more feminine than anyone else,” said Ms. Padgett, the onetime New York City Ballet dancer. “There have been so many times when I’ve been on the street and I realize I’m the only one in a dress and heels. I reach for those things that are more feminine than a genetic girl would go for. The stakes are higher for me because I wasn’t born female so I don’t take it for granted.”

Ms. James of St. Louis agrees: “I feel naked if I don’t have eye makeup on. I’ve worked hard to get this far.”

Nearly all older trans men have experienced oppression, but they had the advantage of growing up in an era when coveting manhood was somewhat understandable and tomboyishness was at least forgiven.

Jeffrey Dickemann, an 85-year-old retired anthropology professor from Sonoma State University in California who transitioned in his 60s, recalls that when he was in college, there were rules against women wearing trousers. But he also had a dad who bonded with him over sports and clothes. “In high school, my father gave me his military boots, which I wore,” he said. “I didn’t even realize how much I stuck out.”

Katherine Rachlin, a therapist who counsels trans people, said these themes come up frequently. “It’s much more difficult if you’re a woman that is 6-foot-3 than a man who is 5-foot-3,” she said. “We look at women differently.”

This also resonates with Vanessa Fabbre, an assistant professor at the Brown School of Social Work at Washington University in St. Louis, and one of the few experts on the subject of late transitioners. “I hear a lot of older trans men say that they were tomboys and that it was acceptable,” she said. “But we don’t have an equivalent term for tomboy with people who are born male. We have yet to create a real option for young boys wanting to express an aspect of their female selves.”

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The lives of late-age transitioners have been documented on a website, To Survive on This Shore, by Vanessa Fabbre and her life partner, Jess T. Dugan. Among those featured are, clockwise from upper left, Mickey Mahoney, 61; Stephanie James, 64; Eugene Potchen-Webb, 60; Bobbi Swan, 84; Helena Bushong, 63; Connor Maddocks, 62.

Three years ago, Ms. Fabbre was studying for a doctoral degree in social sciences at the University of Chicago, when she decided to write her thesis on late-age transitioners. With Jess T. Dugan, 28, a photographer who is also her life partner, Ms. Fabbre has been documenting the lives of many of these people on a website called To Survive on This Shore. However ostracized and exoticized they are, perhaps the most shocking thing about their pictures on the site is how ordinary the people in them seem.

“I could just tell,” she said. “I kept saying, ‘I think he’s transitioning.’ He was taking all the actions I took. But I can’t imagine what it must be like to be him. People have said to me over and over ‘What you’re doing is so brave.’ But I never felt it had anything to do with braveness. It was a need and a hunger, and when I saw the solution it was like a truckload of food coming at a starving person. Someone like Bruce Jenner has to do it in front of the entire world. That is brave.”

Occasionally, she has noticed the sneering tone of some of the tabloid coverage, the incredulity that someone could have hidden this for so long and decided so late to take action. But that’s exactly why she thinks it will be a watershed moment.

“It’s going to spotlight these issues to millions of Americans,” Ms. Padgett said. “It shows that whatever body you’re born into, being transgender doesn’t go away. I thought it wasn’t going to last, the desire to be female would go away. If anything, at 50 it got stronger. And then it was like ‘what the hell.’ I’ve only got a few more years. Why not do what I’ve always wanted to do?”